(3E)-1,1,1-Tri­chloro-4-meth­­oxy-4-phenyl­but-3-en-2-one

The title compound, C₁₁H₉Cl₃O₂, (common name: β-aryl-β-meth­oxy­vinyl tri­chloro­methyl­ketone) was crystallized from a chloro­form solution at room temperature. The asymmetric unit comprises one mol­ecule with all atoms in general positions and the E isomerism about the central vinyl entity could be undoubtedly determined. Weak intra­molecular inter­actions between the ketone and the phenyl groups can be suggested, as two O⋯C distances [2.9154 (17) and 2.9780 (15) Å] are shorter than the van der Waals radii sum for the respective atoms (3.35 Å). As a result of the sp³ C atoms and the C—C single bond between the phenyl ring and the central alkene fragment, the mol­ecule is not planar. In the crystal, the mol­ecules are linked by Cl⋯O weak inter­actions along the a-axis direction (2.962 Å inter­molecular distances, compared to the 3.34 Å for the vdW radius sum) and these contacts were observed over the Hirshfeld surfaces set as d_norm, shape-index and curvedness modes. The Hirshfeld surface analysis mapped over the d_norm property indicates that four major contributions for the crystal cohesion are the H⋯Cl/Cl⋯H (34.2%), H⋯H (22.2%), H⋯C/C⋯H (13.5%) and H⋯O/O⋯H (10.6%) contacts. In addition, quantum-mechanical properties were calculated using the B3LYP/6–31 G(d,p) monomer wavefunctions model. The calculations were performed from a single mol­ecular entity within a radial cluster of symmetry-generated mol­ecules, with the radius set to 3.8 Å, and the total inter­molecular energies between the mol­ecular pairs range from −3.5 kJ/mol to −22.4 kJ mol⁻¹. An expanded structure section, set to 3 × 3 × 3 unit cells, was used for the visualization of the energy-framework (only the total energy property was selected and the energy cut-off was set to 10.0 kJ/mol). The synthesis and ¹H/¹³C NMR data of the title compound are already published in the literature [Siqueira et al. (1994). Quim. Nova, 17, 24–26].

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Chemical scheme

Structure description

The title compound, β-aryl-β-meth­oxy­vinyl tri­chloro­methyl­ketone, belongs to the chemical class of alk­oxy­vinyl ketones, which are employed as starting materials or building blocks in heterocyclic chemistry (Druzhinin et al., 2007; Martins et al., 2008; Mittersteiner et al., 2020; Nenajdenko et al., 1997 & Vashchenko et al., 2022). To the best of our knowledge, following a structural search with SciFinder (Chemical Abstracts Service, 2025), which returned over 50 results, the title compound was first obtained and characterized through ¹H and ¹³C NMR spectroscopy by Siqueira et al. (1994).

Herein, as part of our inter­est in the chemical structure of reaction inter­mediates and educts for organic synthetic chemistry, we report the crystal structure and Hirshfeld analysis of the title alk­oxy­vinyl ketone derivative.

For the title compound, the asymmetric unit matches the mol­ecular structure, with all atoms being located in general positions. The mol­ecule is not planar due to the sp³-hybridized C1 and C11 atoms and due to the single bond between the phenyl and the vinyl fragments, which allows a rotation around the axis through the C4—C5 atoms (Fig. 1), with the torsion angles for the C3—C4—C5—C6 and C3—C4—C5—C10 chains being −51.87 (18) and 131.55 (14)°, respectively. Concerning the C3—C4 vinyl entity, the E isomer could be indubitably determined. It is important to remark that the E/Z isomerism for some meth­oxy­vinyl ketone derivatives, including natural products, is determined by kinetic and thermodynamic parameters, where the Z isomer is thermodynamically unstable and the E isomer is preferred (Kiuchi et al., 1990).

Figure 1 The mol­ecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 40% probability level.

In addition, intra­molecular inter­actions for the title compound are observed. The distances between the O1 atom of the ketone group and the C5 and C6 atoms of the phenyl ring amount to 2.9780 (15) and 2.9154 (17) Å (Fig. 2), being shorter than the sum of the van der Waals radii for the respective atoms (3.35 Å; Batsanov, 2001; Rowland & Taylor, 1996).

Figure 2 The mol­ecular structure of the title compound showing the O1⋯C5 and O1⋯C6 intra­molecular inter­actions. The inter­actions are drawn as dashed lines and the inter­atomic distances are indicated within the figure. This distances are shorter than the sum of the van der Waals radii for O and C (3.35 Å).

In the crystal, the mol­ecules are connected by weak inter­molecular Cl⋯O inter­actions along [100] and build a one-dimensional supra­molecular arrangement (Fig. 3). The Cl⋯O distances amount to 2.9620 (11) Å, while the sum of the vdW radii for the respective atoms is 3.34 Å (Batsanov, 2001; Rowland & Taylor, 1996). Otherwise, only very weak inter­molecular inter­actions, e.g., London dispersion forces can be presumed. There are four mol­ecules in the unit cell and one graphical analysis with Mercury 4.0 (Macrae et al., 2020) reveals that all of them have their centres of gravity located on two glide planes. For a better understanding of the unit cell, a colour-coded system was used for the figure, as follows: the asymmetric unit was drawn in grey, the mol­ecule generated through an inversion centre was drawn in yellow, the mol­ecule generated through a twofold rotoinversion axis was drawn in green and the last one, generated by a glide plane, was drawn in pink (Fig. 4).

Figure 3 Part of the crystal structure of the title compound showing the O1⋯Cl2 inter­molecular contacts as dashed lines. The O1⋯Cl2 distances amount to 2.9620 (11) Å and are shorter than the vdW radii sum for O and Cl atoms, which is 3.34 Å. [Symmetry codes: (i) x − 1, y, z; (ii) x + 1, y, z.]

Figure 4 Graphical representation of the unit cell of the title compound. The mol­ecules within the unit cell are colour-coded: grey for the asymmetric unit, yellow for the mol­ecule generated through an inversion centre, green for the mol­ecule generated through a twofold rotoinversion axis and pink for the mol­ecule generated through a glide plane.

The Hirshfeld surface analysis (Hirshfeld, 1977), the graphical representations and the two-dimensional Hirshfeld surface fingerprints (HSFP) of the crystal structure were performed with Crystal Explorer 21 (Spackman et al., 2021). The first graphical representation of the Hirshfeld surface was set to the d_norm property and the regions with strongest inter­mol­ecular contacts, i.e., the regions around the O1 and Cl2 atoms are indicated in red (Fig. 5). These atoms are those involved in the inter­molecular inter­actions shown in Fig. 3. This analysis indicates that the four most relevant inter­molecular inter­actions for crystal cohesion are the following: H⋯Cl/Cl⋯H (34.2%), H⋯H (22.2%), H⋯C/C⋯H (13.5%) and H⋯O/O⋯H (10.6%). The cited contributions to the crystal packing are shown as two-dimensional Hirshfeld surface fingerprint plots (HSFP) with cyan dots. Minor contributions to the crystal packing are the Cl⋯Cl (6.7%), C⋯Cl/Cl⋯C (5.7%) and Cl⋯O/O⋯Cl (5.5%), and are drawn in all graphics as grey dots (Fig. 6). The second graphical representation of the Hirshfeld surface was set to the shape-index property, in which the locations of the strongest inter­molecular contacts are shown as concave red drawn surfaces, that indicate acceptor atoms, and convex blue drawn surfaces, that indicate the donor atoms involved in inter­molecular inter­actions. For this surface analysis, the regions around the O1 and Cl2 atoms are the most important, geometrically (concave/convex) and by colour intensity (red/blue) (Fig. 7) and concur with the previous figures (Figs. 3 and 5). The last graphical representation of the Hirshfeld surface was set to the curvedness property. For this property, flat surface regions favour inter­molecular contacts, while irregularities or vertices preclude short-range inter­molecular forces. The surface regions around the O1 and Cl2 atoms are flat and proper to the inter­molecular inter­actions between the mol­ecules (Fig. 8) and this information agrees with the previous analysis and Figures (Figs. 3, 6 and 7). In contrast, the surface over the phenyl ring is irregular and shows vertices, which precludes inter­molecular inter­actions, e. g., the π-stacking with this entities. For details of the Hirshfeld surface properties, see: Spackman & Jayatilaka (2009).

Figure 5 Two independent views for the graphical representation of the Hirshfeld surface of the title compound mapped over dnorm. The surfaces are drawn with transparency, the mol­ecules are drawn using a ball-and-stick model and the regions with strongest inter­molecular contacts are shown in red (corresponding to the O1 and Cl2 atom positions).

Figure 6 The Hirshfeld surface two-dimensional fingerprint plot (HSFP) for the title compound, showing the contacts in detail (cyan dots). The major contributions to the crystal cohesion are the following inter­actions: H⋯Cl/Cl⋯H (34.2%), H⋯H (22.2%), H⋯C/C⋯H (13.5%) and H⋯O/O⋯H (10.6%). All the minor contributions are not specified and drawn in grey. The di (x-axis) and the de (y-axis) values are the closest inter­nal and external distances from given points on the Hirshfeld surface (in Å).

Figure 7 Two independent views for the graphical representation of the Hirshfeld surface of the title compound mapped over shape-index. The surfaces are drawn with transparency, the mol­ecules are drawn using a ball-and-stick model and the regions with strongest inter­molecular contacts are shown in dark red/concave (Cl2) and dark blue/convex (O1) colour/surface geometry.

Figure 8 Two independent views for the graphical representation of the Hirshfeld surface of the title compound mapped over curvedness. The surfaces are drawn with transparency, the mol­ecules are drawn using a ball-and-stick model and the locations suitable for inter­molecular contacts are shown as flats regions, e. g., the regions around the O1 and Cl2 atoms.

The inter­action energies between the mol­ecules in the crystal structure were performed with the monomer wavefunctions B3LYP/6–31 G(d,p) model that is embedded in the Crystal Explorer 21 (Spackman et al., 2021). For the calculation of the energies, a radial cluster of 3.8 Å around the asymmetric unit was generated (Fig. 9). The total energy (E_tot) between pairs of mol­ecules (N) rage from −3.5 to −22.4 kJ mol⁻¹ and is a result of four energy components, viz. the electrostatic (E_ele, which ranges from −0.8 to −10.6 kJ mol⁻¹, polarization (E_pol, −0.2 to −2.9 kJ mol⁻¹) , dispersion (E_dis, −3.1 to −27.2 kJ mol⁻¹) , and exchange-repulsion (E_dis, 0.5 to 24.6 kJ mol⁻¹ contributions. The number of mol­ecule pairs (N), the symmetry operations for those (Symop), the distance between the mol­ecular centroids (R; in Å) and the energy components (in kJ mol⁻¹) are given within the Figure. Finally, an energy framework for a crystal section of 3 × 3 × 3 unit cells was performed. The total energy of the section is drawn as cylinder mode in blue and set to 150 reference units. For the graphic, a total energy cut-off was set to 10 kJ mol⁻¹ for clarity (Fig. 10). All the energy and symmetry parameters were based on the atomic coordinates and do not correspond to the centre of mass of the mol­ecules (Mackenzie et al., 2017; Spackman et al., 2021).

Figure 9 (a) Graphical representation of the radial cluster of 3.8 Å around the asymmetric unit, which lies in the centre of the picture and is drawn in black. The symmetry-generated mol­ecules are colour-coded and the figure is simplified for clarity. (b) The box generated by Crystal Explorer 21 (Spackman et al., 2021) with the following data: the colour-codes of the mol­ecule pairs (N), the symmetry operations (Symop), the distance between the mol­ecular centroids (R, in Å) and the energy components (in kJ mol^−1).

Figure 10 Graphical representation of the energy framework for a crystal section of 3 × 3 × 3 unit cells of the title compound viewed along [100]. The total energy is represented as cylinder mode in blue and set to 150 reference units. For clarity, the total energy cut-off was set to 10.0 kJ mol^−1.

From a database survey with the Cambridge Structural Database (CSD, accessed via WebCSD on November 23, 2025; Groom et al., 2016) and the CONQUEST software (Version 2025.2.0, accessed on November 23, 2025; Bruno et al., 2002), two similar compounds were selected for comparison with the title compound: E-β-meth­oxy­chalcone (CSD refode, SILFIC; No. 1259317) and Z-β-meth­oxy­chalcone (SILFEY; 1259316), both reported by Kiuchi et al. (1990).

In the asymmetric unit of the E-β-meth­oxy­chalcone derivative, intra­molecular inter­actions between the ketone and the phenyl entities are observed (Fig. 11). The O2⋯C1 and O2⋯C2 distances amount to 2.972 Å and 3.074 Å, being shorter than the sum of the van der Waals radii for the respective atoms of 3.35 Å (Batsanov, 2001; Rowland & Taylor, 1996). The E isomer observed for the C7—C8 central vinyl fragment and the O⋯C intra­molecular inter­actions are quite similar to those for the title compound (Fig. 2).

Figure 11 Mol­ecular structure of a reference compound, the E-β-meth­oxy­chalcone derivative. As for the structure of the title compound, intra­molecular inter­actions between the O2 atom of the ketone group and the C1 and C2 atoms of the phenyl ring are observed. The inter­actions are drawn as dashed lines and the inter­atomic distances are given within the figure (in Å), being shorter than the sum of the van der Waals radii for O and C (3.34 Å).

For the Z-β-meth­oxy­chalcone derivative, an intra­molecular inter­action is observed between the ketone and the methyl entities (Fig. 12). The O2⋯H13 distance amounts to 2.177 Å, which is a value shorter then the van der Waals reference radii for the selected atoms of 2.68 Å (Batsanov, 2001; Rowland & Taylor, 1996). The Z isomer observed for the C7—C8 central vinyl fragment is thermodynamically unstable and tends to isomerize to the E isomer, as observed for natural β-meth­oxy­chalcone derivatives (Kiuchi et al., 1990). As observed in the structure of the title compound, a rotation of the phenyl ring bonded to the central vinyl entity is possible due to the C—C simple bond between the two groups (C4—C5 for the title compound, Figs. 1–3; C1—C7 for the reference E/Z-β-meth­oxy­chalcone derivatives, Figs. 11 and 12).

Figure 12 Mol­ecular structure of a second reference compound, the Z-β-meth­oxy­chalcone derivative. For this isomer, an intra­molecular inter­action between the O2 atom of the ketone group and the H13 atom of the methyl fragment are observed. The inter­action is drawn as a dashed linesand the inter­atomic distance is given within the figure (in Å), being shorter than the sum of the van der Waals radii for O and H (2.68 Å).

Synthesis and crystallization

The synthesis of the title compound is already reported in the literature (Siqueira et al., 1994). Colourless single crystals suitable for X-ray diffraction were obtained from a solution in chloro­form at room temperature by slow evaporation of the solvent.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C11H9Cl3O2
Mr	279.53
Crystal system, space group	Monoclinic, P21/n
Temperature (K)	200
a, b, c (Å)	6.2726 (3), 9.7791 (4), 19.7780 (9)
β (°)	98.368 (1)
V (Å^3)	1200.27 (9)
Z	4
Radiation type	Mo Kα
μ (mm^−1)	0.74
Crystal size (mm)	0.40 × 0.22 × 0.18
Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (Krause et al., 2015)
Tmin, Tmax	0.704, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14717, 4368, 3767
Rint	0.015
(sin θ/λ)max (Å^−1)	0.758
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.033, 0.088, 1.07
No. of reflections	4368
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å^−3)	0.43, −0.34
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXT2014/5 (Sheldrick, 2015a), SHELXL2019/2 (Sheldrick, 2015b), DIAMOND (Brandenburg, 2006), Crystal Explorer 21 (Spackman et al., 2021), Mercury (Macrae et al., 2020), WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and enCIFer (Allen et al., 2004).

Structural data

Computing details

(3E)-1,1,1-Trichloro-4-methoxy-4-phenylbut-3-en-2-one

Crystal data

C11H9Cl3O2	Dx = 1.547 Mg m^−3
Mr = 279.53	Melting point = 358.15–359.15 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2726 (3) Å	Cell parameters from 7757 reflections
b = 9.7791 (4) Å	θ = 3.0–32.6°
c = 19.7780 (9) Å	µ = 0.74 mm^−1
β = 98.368 (1)°	T = 200 K
V = 1200.27 (9) Å^3	Fragment, colourless
Z = 4	0.40 × 0.22 × 0.18 mm
F(000) = 568

Data collection

Bruker APEXII CCD diffractometer	4368 independent reflections
Radiation source: fine-focus sealed X-ray tube, Bruker APEXII CCD diffractometer	3767 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.015
φ and ω scans	θmax = 32.6°, θmin = 2.1°
Absorption correction: multi-scan (Krause et al., 2015)	h = −7→9
Tmin = 0.704, Tmax = 0.746	k = −14→10
14717 measured reflections	l = −29→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0354P)^2 + 0.5708P] where P = (Fo^2 + 2Fc^2)/3
4368 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms were located in a difference map and refined as riding on their parent atom with C_methyl—H = 0.98 Å and with U(H)=1.5U_eq(C_methyl) or with C—H = 0.95 Å and with U(H)=1.2U_eq(C) for the remaining H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.43349 (19)	0.41558 (12)	0.72330 (6)	0.0251 (2)
C2	0.56268 (18)	0.36450 (13)	0.66578 (6)	0.0247 (2)
C3	0.51636 (19)	0.22363 (13)	0.64522 (6)	0.0263 (2)
H3	0.414874	0.175059	0.667306	0.032*
C4	0.60816 (19)	0.15658 (12)	0.59660 (6)	0.0246 (2)
C5	0.74087 (19)	0.21757 (12)	0.54826 (6)	0.0247 (2)
C6	0.6678 (2)	0.32986 (14)	0.50812 (7)	0.0317 (3)
H6	0.532750	0.370289	0.512480	0.038*
C7	0.7922 (3)	0.38262 (15)	0.46180 (7)	0.0382 (3)
H7	0.741795	0.459059	0.434399	0.046*
C8	0.9898 (3)	0.32441 (16)	0.45525 (7)	0.0387 (3)
H8	1.075848	0.362076	0.424137	0.046*
C9	1.0613 (2)	0.21143 (17)	0.49412 (8)	0.0385 (3)
H9	1.195835	0.170859	0.489269	0.046*
C10	0.9366 (2)	0.15695 (15)	0.54035 (7)	0.0322 (3)
H10	0.985093	0.078485	0.566474	0.039*
C11	0.4704 (3)	−0.05854 (15)	0.62909 (8)	0.0388 (3)
H11A	0.534594	−0.045215	0.676845	0.058*
H11B	0.478284	−0.155469	0.617122	0.058*
H11C	0.319339	−0.029421	0.623042	0.058*
Cl1	0.50590 (7)	0.58393 (4)	0.74788 (2)	0.04314 (10)
Cl2	0.15408 (5)	0.40992 (3)	0.69129 (2)	0.03038 (8)
Cl3	0.48876 (6)	0.30748 (4)	0.79602 (2)	0.03966 (9)
O1	0.68633 (17)	0.44382 (11)	0.64506 (6)	0.0378 (2)
O2	0.58644 (17)	0.02147 (10)	0.58544 (5)	0.0331 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0256 (5)	0.0257 (5)	0.0241 (5)	0.0021 (4)	0.0039 (4)	−0.0018 (4)
C2	0.0203 (4)	0.0284 (5)	0.0256 (5)	0.0021 (4)	0.0037 (4)	−0.0026 (4)
C3	0.0257 (5)	0.0260 (5)	0.0286 (5)	0.0002 (4)	0.0089 (4)	−0.0014 (4)
C4	0.0262 (5)	0.0239 (5)	0.0241 (5)	0.0018 (4)	0.0050 (4)	0.0005 (4)
C5	0.0264 (5)	0.0256 (5)	0.0227 (5)	0.0003 (4)	0.0061 (4)	−0.0017 (4)
C6	0.0381 (6)	0.0290 (6)	0.0292 (6)	0.0043 (5)	0.0094 (5)	0.0025 (5)
C7	0.0548 (9)	0.0325 (7)	0.0293 (6)	−0.0038 (6)	0.0125 (6)	0.0032 (5)
C8	0.0467 (8)	0.0417 (7)	0.0311 (6)	−0.0158 (6)	0.0173 (6)	−0.0087 (5)
C9	0.0306 (6)	0.0471 (8)	0.0407 (7)	−0.0043 (6)	0.0146 (5)	−0.0105 (6)
C10	0.0285 (6)	0.0349 (6)	0.0342 (6)	0.0039 (5)	0.0084 (5)	−0.0016 (5)
C11	0.0493 (8)	0.0279 (6)	0.0426 (7)	−0.0057 (6)	0.0184 (6)	0.0018 (5)
Cl1	0.0509 (2)	0.03137 (16)	0.0484 (2)	−0.00447 (14)	0.01142 (16)	−0.01452 (14)
Cl2	0.02343 (13)	0.03637 (16)	0.03254 (15)	0.00427 (11)	0.00811 (10)	0.00448 (11)
Cl3	0.0482 (2)	0.04573 (19)	0.02411 (14)	0.00755 (15)	0.00210 (12)	0.00613 (12)
O1	0.0345 (5)	0.0373 (5)	0.0452 (6)	−0.0106 (4)	0.0181 (4)	−0.0084 (4)
O2	0.0453 (5)	0.0237 (4)	0.0334 (5)	−0.0016 (4)	0.0164 (4)	−0.0019 (3)

Geometric parameters (Å, º)

C1—C2	1.5711 (16)	C6—H6	0.9500
C1—Cl1	1.7575 (12)	C7—C8	1.387 (2)
C1—Cl2	1.7755 (12)	C7—H7	0.9500
C1—Cl3	1.7780 (12)	C8—C9	1.383 (2)
C2—O1	1.2098 (15)	C8—H8	0.9500
C2—C3	1.4536 (17)	C9—C10	1.393 (2)
C3—C4	1.3593 (16)	C9—H9	0.9500
C3—H3	0.9500	C10—H10	0.9500
C4—O2	1.3432 (15)	C11—O2	1.4388 (17)
C4—C5	1.4814 (16)	C11—H11A	0.9800
C5—C10	1.3926 (17)	C11—H11B	0.9800
C5—C6	1.3930 (18)	C11—H11C	0.9800
C6—C7	1.3864 (19)
C2—C1—Cl1	111.00 (8)	C5—C6—H6	120.0
C2—C1—Cl2	108.56 (8)	C6—C7—C8	120.36 (14)
Cl1—C1—Cl2	109.25 (6)	C6—C7—H7	119.8
C2—C1—Cl3	109.65 (8)	C8—C7—H7	119.8
Cl1—C1—Cl3	108.72 (6)	C9—C8—C7	119.86 (13)
Cl2—C1—Cl3	109.64 (7)	C9—C8—H8	120.1
O1—C2—C3	128.67 (11)	C7—C8—H8	120.1
O1—C2—C1	117.71 (11)	C8—C9—C10	120.20 (13)
C3—C2—C1	113.62 (10)	C8—C9—H9	119.9
C4—C3—C2	124.54 (11)	C10—C9—H9	119.9
C4—C3—H3	117.7	C9—C10—C5	119.96 (13)
C2—C3—H3	117.7	C9—C10—H10	120.0
O2—C4—C3	123.20 (11)	C5—C10—H10	120.0
O2—C4—C5	110.06 (10)	O2—C11—H11A	109.5
C3—C4—C5	126.73 (11)	O2—C11—H11B	109.5
C10—C5—C6	119.60 (12)	H11A—C11—H11B	109.5
C10—C5—C4	119.25 (11)	O2—C11—H11C	109.5
C6—C5—C4	121.06 (11)	H11A—C11—H11C	109.5
C7—C6—C5	119.98 (13)	H11B—C11—H11C	109.5
C7—C6—H6	120.0	C4—O2—C11	118.97 (10)
Cl1—C1—C2—O1	−1.68 (14)	O2—C4—C5—C6	127.31 (13)
Cl2—C1—C2—O1	118.42 (11)	C3—C4—C5—C6	−51.87 (18)
Cl3—C1—C2—O1	−121.83 (11)	C10—C5—C6—C7	−1.5 (2)
Cl1—C1—C2—C3	177.58 (8)	C4—C5—C6—C7	−178.10 (13)
Cl2—C1—C2—C3	−62.32 (11)	C5—C6—C7—C8	−0.2 (2)
Cl3—C1—C2—C3	57.44 (12)	C6—C7—C8—C9	1.3 (2)
O1—C2—C3—C4	−0.7 (2)	C7—C8—C9—C10	−0.7 (2)
C1—C2—C3—C4	−179.88 (11)	C8—C9—C10—C5	−1.0 (2)
C2—C3—C4—O2	170.12 (12)	C6—C5—C10—C9	2.1 (2)
C2—C3—C4—C5	−10.8 (2)	C4—C5—C10—C9	178.73 (12)
O2—C4—C5—C10	−49.27 (15)	C3—C4—O2—C11	−3.44 (19)
C3—C4—C5—C10	131.55 (14)	C5—C4—O2—C11	177.35 (12)